CN102858719B - 用于催化剂再生以及延长使用的方法 - Google Patents
用于催化剂再生以及延长使用的方法 Download PDFInfo
- Publication number
- CN102858719B CN102858719B CN201180020221.XA CN201180020221A CN102858719B CN 102858719 B CN102858719 B CN 102858719B CN 201180020221 A CN201180020221 A CN 201180020221A CN 102858719 B CN102858719 B CN 102858719B
- Authority
- CN
- China
- Prior art keywords
- catalyst
- alkylation
- catalyzer
- beta
- reactor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 232
- 238000000034 method Methods 0.000 title claims abstract description 76
- 230000008929 regeneration Effects 0.000 title claims abstract description 33
- 238000011069 regeneration method Methods 0.000 title claims abstract description 33
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 239
- 230000029936 alkylation Effects 0.000 claims abstract description 228
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 114
- 238000006243 chemical reaction Methods 0.000 claims abstract description 80
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 54
- 230000009849 deactivation Effects 0.000 claims abstract description 23
- 230000002152 alkylating effect Effects 0.000 claims abstract description 17
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 9
- 238000011144 upstream manufacturing Methods 0.000 claims abstract description 4
- 229910021536 Zeolite Inorganic materials 0.000 claims description 35
- 239000010457 zeolite Substances 0.000 claims description 35
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 27
- 231100000614 poison Toxicity 0.000 claims description 27
- 230000002779 inactivation Effects 0.000 claims description 26
- 239000002574 poison Substances 0.000 claims description 26
- 230000000694 effects Effects 0.000 claims description 15
- 230000008569 process Effects 0.000 abstract description 24
- 230000002829 reductive effect Effects 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 description 21
- 238000000926 separation method Methods 0.000 description 20
- 238000010555 transalkylation reaction Methods 0.000 description 17
- -1 alkylaryl hydrocarbons Chemical class 0.000 description 11
- 229930195733 hydrocarbon Natural products 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000007791 liquid phase Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002808 molecular sieve Substances 0.000 description 6
- 230000000630 rising effect Effects 0.000 description 6
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 5
- 238000010926 purge Methods 0.000 description 5
- 230000001172 regenerating effect Effects 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 238000003442 catalytic alkylation reaction Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000007600 charging Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011066 ex-situ storage Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000006069 physical mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000000739 chaotic effect Effects 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/067—C8H10 hydrocarbons
- C07C15/073—Ethylbenzene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/765,119 | 2010-04-22 | ||
| US12/765,119 US8455383B2 (en) | 2009-09-28 | 2010-04-22 | Process for catalyst regeneration and extended use |
| PCT/US2011/026623 WO2011133250A1 (en) | 2010-04-22 | 2011-03-01 | Process for catalyst regeneration and extended use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102858719A CN102858719A (zh) | 2013-01-02 |
| CN102858719B true CN102858719B (zh) | 2015-11-25 |
Family
ID=43781075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180020221.XA Active CN102858719B (zh) | 2010-04-22 | 2011-03-01 | 用于催化剂再生以及延长使用的方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8455383B2 (ja) |
| EP (1) | EP2560934A4 (ja) |
| JP (1) | JP5739519B2 (ja) |
| KR (1) | KR101811373B1 (ja) |
| CN (1) | CN102858719B (ja) |
| BR (1) | BR112012026918B1 (ja) |
| CA (1) | CA2796291C (ja) |
| EA (1) | EA024270B1 (ja) |
| SG (1) | SG184476A1 (ja) |
| TW (1) | TWI499454B (ja) |
| WO (1) | WO2011133250A1 (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8865958B2 (en) * | 2008-09-30 | 2014-10-21 | Fina Technology, Inc. | Process for ethylbenzene production |
| US8420877B2 (en) | 2008-09-30 | 2013-04-16 | Fina Technology, Inc. | Process for ethylbenzene production |
| US8455383B2 (en) | 2009-09-28 | 2013-06-04 | Fina Technology, Inc. | Process for catalyst regeneration and extended use |
| JP2014518857A (ja) * | 2011-05-02 | 2014-08-07 | フイナ・テクノロジー・インコーポレーテツド | エチルベンゼンの製法 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3308069A (en) | 1964-05-01 | 1967-03-07 | Mobil Oil Corp | Catalytic composition of a crystalline zeolite |
| US4101596A (en) | 1977-01-10 | 1978-07-18 | Mobil Oil Company | Low pressure xylene isomerization |
| US4642226A (en) | 1984-04-16 | 1987-02-10 | Mobil Oil Corporation | Process for the preparation of zeolite Beta using dibenzyldimethylammonium ions and the product produced |
| US5081323A (en) | 1987-12-17 | 1992-01-14 | Chevron Research And Technology Company | Liquid phase alkylation or transalkylation process using zeolite beta |
| US5227558A (en) | 1992-02-10 | 1993-07-13 | Fina Technology, Inc. | Aromatic alkylation process employing steam modified zeolite beta catalyst |
| EP0571701A1 (en) | 1992-05-20 | 1993-12-01 | Fina Research S.A. | Process for the alkylation of aromatics |
| US5362697A (en) | 1993-04-26 | 1994-11-08 | Mobil Oil Corp. | Synthetic layered MCM-56, its synthesis and use |
| US5489732A (en) | 1994-10-14 | 1996-02-06 | Uop | Fluidized solid bed motor fuel alkylation process |
| CN1088049C (zh) * | 1996-05-29 | 2002-07-24 | 埃克森美孚化学专利公司 | 芳烃转化方法和适用的沸石催化剂 |
| US5723710A (en) | 1996-07-12 | 1998-03-03 | Uop | Zeolite beta and its use in aromatic alkylation |
| WO1998003455A1 (fr) | 1996-07-19 | 1998-01-29 | Asahi Kasei Kogyo Kabushiki Kaisha | Procede pour la preparation d'ethylbenzene |
| DE69705958T2 (de) | 1996-09-06 | 2002-04-04 | Exxon Chemical Patents, Inc. | Alkylierungsverfahren in dem zeolith beta verwendet wird |
| IT1290846B1 (it) | 1996-12-12 | 1998-12-14 | Enichem Spa | Composizione catalitica e processo per l'alchilazione e/o la transalchilazione di composti aromatici |
| US5907073A (en) | 1998-02-24 | 1999-05-25 | Fina Technology, Inc. | Aromatic alkylation process |
| US6559428B2 (en) | 2001-01-16 | 2003-05-06 | General Electric Company | Induction heating tool |
| AU2001240077A1 (en) * | 2000-05-19 | 2001-12-03 | Channelogics, Inc. | Allocating access across shared communications medium |
| US6781025B2 (en) | 2001-07-11 | 2004-08-24 | Exxonmobil Chemical Patents Inc. | Reactivation of aromatics alkylation catalysts |
| WO2003074452A1 (en) | 2002-02-28 | 2003-09-12 | Stone & Webster, Inc. | Production of alkyl aromatic compounds |
| US7268264B2 (en) | 2002-10-04 | 2007-09-11 | Fina Technology, Inc. | Critical phase alkylation process |
| US6987078B2 (en) | 2003-10-03 | 2006-01-17 | Fina Technology, Inc. | Alkylation and catalyst regenerative process |
| US7297827B2 (en) | 2004-11-29 | 2007-11-20 | Fina Technology, Inc. | Use of monolith catalyst to prepare ethylbenzene |
| US20070161835A1 (en) | 2006-01-07 | 2007-07-12 | Fina Technology, Inc. | Liquid phase alkylation system |
| US7495139B2 (en) | 2006-01-07 | 2009-02-24 | Fina Technology, Inc. | Use of modified zeolite catalysts in alkylation systems |
| BRPI0706421A2 (pt) | 2006-01-07 | 2011-03-29 | Fina Technology | alquilação em fase lìquida diluìda |
| US20080058568A1 (en) | 2006-09-05 | 2008-03-06 | Fina Technology, Inc. | Processes for the reduction of alkylation catalyst deactivation utilizing stacked catalyst bed |
| US20080058566A1 (en) | 2006-09-05 | 2008-03-06 | Fina Technology, Inc. | Processes for reduction of alkylation catalyst deactivation utilizing low silica to alumina ratio catalyst |
| US7790940B2 (en) | 2007-06-21 | 2010-09-07 | Exxonmobil Chemical Patents Inc. | Liquid phase alkylation process |
| US8865958B2 (en) * | 2008-09-30 | 2014-10-21 | Fina Technology, Inc. | Process for ethylbenzene production |
| US8455383B2 (en) | 2009-09-28 | 2013-06-04 | Fina Technology, Inc. | Process for catalyst regeneration and extended use |
-
2010
- 2010-04-22 US US12/765,119 patent/US8455383B2/en active Active
-
2011
- 2011-02-15 TW TW100104928A patent/TWI499454B/zh not_active IP Right Cessation
- 2011-03-01 EA EA201270762A patent/EA024270B1/ru not_active IP Right Cessation
- 2011-03-01 CA CA2796291A patent/CA2796291C/en not_active Expired - Fee Related
- 2011-03-01 BR BR112012026918-6A patent/BR112012026918B1/pt not_active IP Right Cessation
- 2011-03-01 CN CN201180020221.XA patent/CN102858719B/zh active Active
- 2011-03-01 JP JP2013506146A patent/JP5739519B2/ja not_active Expired - Fee Related
- 2011-03-01 EP EP11772379.1A patent/EP2560934A4/en not_active Withdrawn
- 2011-03-01 WO PCT/US2011/026623 patent/WO2011133250A1/en active Application Filing
- 2011-03-01 KR KR1020127028079A patent/KR101811373B1/ko active IP Right Grant
- 2011-03-01 SG SG2012074332A patent/SG184476A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SG184476A1 (en) | 2012-11-29 |
| KR101811373B1 (ko) | 2017-12-22 |
| CA2796291A1 (en) | 2011-10-27 |
| US20110077443A1 (en) | 2011-03-31 |
| EA201270762A1 (ru) | 2013-03-29 |
| JP5739519B2 (ja) | 2015-06-24 |
| TW201206567A (en) | 2012-02-16 |
| WO2011133250A1 (en) | 2011-10-27 |
| CN102858719A (zh) | 2013-01-02 |
| CA2796291C (en) | 2016-07-05 |
| EP2560934A1 (en) | 2013-02-27 |
| EP2560934A4 (en) | 2015-11-25 |
| BR112012026918A2 (pt) | 2016-07-12 |
| EA024270B1 (ru) | 2016-09-30 |
| TWI499454B (zh) | 2015-09-11 |
| BR112012026918B1 (pt) | 2018-10-23 |
| US8455383B2 (en) | 2013-06-04 |
| JP2013525353A (ja) | 2013-06-20 |
| KR20130064737A (ko) | 2013-06-18 |
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| C06 | Publication | ||
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| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |